Uliginosin B, a phloroglucinol derivative from Hypericum polyanthemum: A promising new molecular pattern for the development of antidepressant drugs

Behavioural Brain Research

Volumn 228, Issue 1, 2012, Pages 66-73

  Stein, Ana C ^a   Viana, Alice F ^a   Müller, Liz G ^a   Nunes, Jéssica M ^a   Stolz, Eveline D ^a   Do Rego, Jean Claude ^b   Costentin, Jean ^b   von Poser, Gilsane L ^a   Rates, Stela M K ^a  

^a FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

^b UNIVERSITÉ DE ROUEN   (France)

Author keywords

Antidepressant; Forced swimming test; Hypericum polyanthemum; Monoaminergic neurotransmission; Uliginosin B

Indexed keywords

8 CHLORO 2,3,4,5 TETRAHYDRO 3 METHYL 5 PHENYL 1H 3 BENZAZEPIN 7 OL HYDROGEN MALEATE; AMFEBUTAMONE; ANTIDEPRESSANT AGENT; CYCLOHEXANE; DOPAMINE; FENCLONINE METHYL ESTER; FLUOXETINE; HYPERICUM POLYANTHEMUM EXTRACT; IMIPRAMINE; NORADRENALIN; PHLOROGLUCINOL DERIVATIVE; PLANT EXTRACT; PRAZOSIN; SEROTONIN; SULPIRIDE; ULIGINOSIN B; UNCLASSIFIED DRUG; YOHIMBINE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTIDEPRESSANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DOPAMINE UPTAKE; DRUG STRUCTURE; FORCED SWIMMING TEST; HYPERICUM; HYPERICUM POLYANTHEMUM; IC 50; IN VITRO STUDY; IN VIVO STUDY; LOCOMOTION; MALE; MONOAMINERGIC SYSTEM; MOUSE; NEUROTRANSMISSION; NONHUMAN; NORADRENALIN UPTAKE; OPEN FIELD TEST; PRIORITY JOURNAL; RAT; SEROTONIN UPTAKE; SYNAPTOSOME;

ANIMALS; ANTIDEPRESSIVE AGENTS; BENZAZEPINES; BIOGENIC MONOAMINES; BUPROPION; DRUG EVALUATION, PRECLINICAL; ENZYME INHIBITORS; FENCLONINE; FLUOXETINE; HYPERICUM; IMIPRAMINE; IMMOBILITY RESPONSE, TONIC; LOCOMOTION; MALE; MICE; MICE, INBRED STRAINS; PHLOROGLUCINOL; PLANT EXTRACTS; PRAZOSIN; RATS; RATS, WISTAR; RECEPTORS, CATECHOLAMINE; SULPIRIDE; VESICULAR MONOAMINE TRANSPORT PROTEINS; YOHIMBINE;

EID: 83655164060     PISSN: 01664328     EISSN: 18727549     Source Type: Journal    
DOI: 10.1016/j.bbr.2011.11.031     Document Type: Article

References (54)

1. Berton O., Nestler E.J. New approaches to antidepressant drug discovery: beyond monoamines. Nat Rev Neurosci 2006, 7:137-141.
2. Kasper S., Caraci F., Forti B., Drago F., Aguglia E. Efficacy and tolerability of Hypericum extract for the treatment of mild to moderate depression. Eur Neuropsychopharmacol 2010, 20:747-765.
3. Nestler E.J., Barrot M., DiLeone R., Eisch A.J., Gold S.J., Monteggia L.M. Neurobiology of depression. Neuron 2002, 34:13-25.
4. Brunello N., Mendlewikz J., Kasper S., Leonard B., Montgomery S., Craig Nelson J., et al. The role of noradrenaline and noradrenaline reuptake inhibitors in depression. Eur Neuropsychopharmacol 2002, 12:461-475.
5. MacGillivray S., Arroll B., Hatcher S., Ogston S., Reid I., Sullivan F., et al. Efficacy and tolerability of selective serotonin reuptake inhibitors compared with tricyclic antidepressants in depression treated in primary care: systematic review and meta-analysis. BMJ 2003, 326:1014-1020.
6. Harvey A.L. Natural products in drug discovery. Drug Discov Today 2008, 13:894-901.
7. ® 5570 after recovery from an acute episode of moderate depression-a double-blind, randomized, placebo controlled long-term trial. Eur Neuropsychopharmacol 2008, 18:803-813.
8. Dall'agnol R., Ferraz A., Bernardi A.P., Albring D., Nör C., Schapoval E.E.S., et al. Bioassay-guided isolation of antimicrobial benzopyrans and phloroglucinol derivatives from Hypericum species. Phytother Res 2005, 19:291-293.
9. Daudt R., von Poser G.L., Neves G., Rates S.M.K. Screnning for the antidepressant activity of some species of Hypericum from South Brazil. Phytother Res 2000, 14:344-346.
10. Ferraz A.B.F., Bordignon S.A.L., Staats C., Schripsema J., von Poser G.L. Benzopyrans from Hypericum polyanthemum. Phytochemistry 2001, 57:1227-1230.
11. Schmitt A.C., Ravazzolo A.P., von Poser G.L. Investigation of some Hypericum species native to Southern of Brazil for antiviral activity. J Ethnopharmacol 2001, 77:239-245.
12. Viana A.F., Heckler A.P., Fenner R., Rates S.M. Antinociceptive activity of Hypericum caprifoliatum and Hypericum polyanthemum (Guttiferae). Braz J Med Biol Res 2003, 36:631-634.
13. Viana A.F., Do Rego J.C., Von Poser G., Ferraz A., Heckler A.P., Costentin J., et al. The antidepressant-like effect of Hypericum caprifoliatum Cham & Schlecht (Guttiferae) on forced swimming test results from an inhibition of neuronal monoamine uptake. Neuropharmacology 2005, 49:1042-1052.
14. Viana A., Do Rego J.C., Munari L., Dourmap N., Heckler A.P., Dalla Costa T., et al. Hypericum caprifoliatum (Guttiferae) Cham & Schltdl.: a species native to South Brazil with antidepressant-like activity. Fundam Clin Pharmacol 2006, 20:507-514.
15. Ferraz A., Bordignon S., Mans D., Schmitt A., Ravazzolo A.P. Screening for the presence of hypericins in southern Brazilian species of Hypericum (Guttiferae). Pharm Biol 2002, 40:294-297.
16. Robson N.K.B. Studies in the genus Hypericum L. (Guttiferae) 8. Sections 29. Brathys (part 2) and 30. Trigynobrathys. Bull Br Mus Nat Hist 1990, 20:1-151.
17. Von Poser G.L., Rech S.B., Rates S.M.K. Chemical and pharmacological aspects of Southern Brazilian Hypericum species. Floriculture, ornamental and plant biotechnology 2006, vol. IV. p. 509-15.
18. Ferraz A.B.F., Schripsema J., Pohlmann A.R., von Poser G.L. Uliginosin B from Hypericum myrianthum Cham & Schltdl. Biochem Syst Ecol 2002, 30:989-991.
19. Gnerre C., Von Poser G.L., Ferraz A., Viana A.F., Testa B., Rates S.M.K. Monoamine oxidase inhibitory activity of some Hypericum species native to South Brazil. J Pharm Pharmacol 2001, 53:1273-1279.
20. Haas J.S., Viana A.F., Heckler A.P.M., Von Poser G.L., Rates S.M.K. The antinociceptive effect of a benzopyran (HP1) Isolated from Hypericum polyanthemum in mice Hot-Plate test is blocked by naloxone. Planta Med 2010, 76:1419-1423.
21. Rocha L., Marston A., Kaplan M.A.C., Stoeckli-Evans H., Thull U., Testa B., et al. An antifungal gamma-pyrone and xanthones wit monoamine oxidase inhibitory activity from Hypericum brasiliense. Phytochemistry 1994, 36:1381-1385.
22. Nör C., Albring D., Ferraz A.B.F., Schripsema J., Pires V., Sonnet P., et al. Phoroglucinol derivatives from four Hypericum species belonging to the Trigynobrathys section. Biochem Syst Ecol 2004, 32:517-519.
23. Nunes J.M., Pinhatti A.V., von Poser G.L., Rech S.B. Promotive effects of long-term fertilization on growth of tissue culture-derived Hypericum polyanthemum plants during acclimatization. Ind Crops Prod 2009, 30:329-332.
24. Brasil 2008. Ministério Público. Lei no. 11.794, de 8 de outubro de 2008. Published in DOU 9.10.2008.
25. Council for International Organizations of Medical Sciences. International guiding principles for biomedical research involving animals, Geneva; 1985.
26. Porsolt R.D., Anton G., Blavet N., Jafre M. Behavioral despair in rats, a new model sensitive to antidepressant treatments. Eur J Pharmacol 1978, 47:379-391.
27. Porsolt R.D., Bertin A., Jalfre M. Behavioral despair in mice: a primary screening test for antidepressants. Arch Int Pharmacodyn Ther 1977, 229:327-336.
28. Cunha M.P., Machado D.G., Bettio L.E.B., Capra J., Rodrigues A.L.S. Interaction of zinc with antidepressants in the tail suspension test. Prog Neuropsychopharmacol Biol Psychiatry 2008, 32:1913-1920.
29. Lobato K.R., Cardoso C.C., Binfare R.W., Budni J., Wagner C.L.R., Brocardo P.S., et al. Alfa-tocopherol administration produces an antidepressant-like effect in predictive animal models of depression. Behav Brain Res 2010, 209:249-259.
30. Wang R., Xu Y., Wu H.L., Li Y.B., Li Y.H., Guo J.B., Li X.J. The antidepressant effect of curcumin in the forced swimming test involve 5-HT1 and 5-HT2 receptors. Eur J Pharmacol 2008, 578:43-50.
31. Lowry O.H., Rosenbrough N.J., Farr A.L., Randall R.J. Protein measurement with the folin phenol reagent. J Biol Chem 1951, 193:265-275.
32. Millan M.J. Multi-target strategies for the improved treatment of depressive states: conceptual foundations and neuronal substrates, drug discovery and therapeutic application. Pharmacol Ther 2006, 110:135-370.
33. Millan M.J. Dual - and triple acting agents for treating core and co-morbid symptoms of major depression: novel concepts, new drugs. Neurotherapeutics 2009, 6:53-77.
34. Breuer M.E., Chan J.S.W., Oosting R.S., Groenink L., Korte S.M., Campbell U., et al. The triple monoaminergic reuptake inhibitor DOV 216, 303 has antidepressant effects in the rat olfactory bulbectomy model and lacks sexual side effects. Eur Neuropsychopharmacol 2008, 18:908-916.
35. Lemke M.R., Brecht H.M., Koester J., Reichman H. Effects of the dopamine agonist pramipexole on depression, anhedonia and motor functioning in Parkinsons disease. J Neurol Sci 2006, 248:266-270.
36. Shankman S.A., Nelson B.D., Harrow M., Faull R. Does physical anhedonia play a role in depression? A 20-year longitudinal study. J Affect Disord 2010, 120:170-176.
37. Chatterjee S.S., Nöldner M., Koch E., Erdelmeier C. Antidepressant activity of Hypericum perforatum and hiperforin: the neglected possibility. Pharmacopsychiatry 1998, 31:7-15.
38. Müller W.E., Singer A., Wonemann M., Hafner U., Rolli M., Schafer C. Hyperforin represents the neurotransmitter reuptake inhibiting constituent of Hypericum extract. Pharmacopsychiatry 1998, 31:16-21.
39. Roz N., Mazur Y., Hirshfeld A., Rehavi M. Inhibition of vesicular uptake of monoamines by hyperforin. Life Sci 2002, 71:2227-2237.
40. Do Rego J.C., Benkiki N., Chosson E., Kabouche Z., Seguin E., Costentin J. Eur J Pharmacol 2007, 569:197-203.
41. Chatterjee S.S., Bhattachrya S.K., Wonnemann M., Singer A., Müller W.E. Hyperforin as a possible antidepressant component of Hypericum extracts. Life Sci 1998, 63:499-510.
42. Jensen A.G., Hansen S.H., Nielsen E.O. Adhyperforin as contributor to the effect of Hypericum perforatum L. in biochemical models of antidepressant activity. Life Sci 2001, 68:593-1605.
43. Appel M., Berfield J.L., Wang L.C., Dunn W.J., Chen N., Reith M.E.A. Structure-activity relationship for substrate recognition by the human dopamine transporter. Biochem Pharmacol 2004, 67:293-302.
44. +. J Pharmacol Exp Ther 1999, 290:1363-1368.
45. Müller W.E., Singer A., Wonnemann M. Hyperforin - antidepressant activity by a novel mechanism of action. Pharmacopsychiatry 2001, 34:98-102.
46. Marsh W.L., Davies J.A. The involvement of sodium and calcium ions in the release of amino acid neurotransmitters from mouse cortical slices elicited by hyperforin. Life Sci 2002, 71:2645-2655.
47. Treiber K., Singer A., Henke B., Muller W.A. Hyperforin activates nonselective cation channels (NSCCs). Br J Pharmacol 2005, 145:75-83.
48. Eckert G.P., Müller W.E. Effects of hyperforin on the fluidity of brain membranes. Pharmacopsychiatry 2001, 34:22-25.
49. Eckert G.P., Keller J.H., Jourdan C., Karas M., Volmer D.A., Schubert-Zsilavecz M.E., et al. Hyperforin modifies neuronal membrane properties in vivo. Neurosci Lett 2004, 367:39-143.
50. Pucadyil T.J., Chattopadhyay A. Role of cholesterol in the function and organization of G-protein coupled receptors. Prog Lipid Res 2006, 45:295-333.
51. Gelb M.H., Brunsveld L., Hrycyna C.A., Michaelis S., Tamanoi F., Van Voorhis W.C., et al. Therapeutic interventions based on protein prenylation and associated modifications. Nat Chem Biol 2006, 2(10):518-528.
52. Rates S.M.K. Plants as source of drugs. Toxicon 2001, 39:603-613.
53. Rollinger J.M., Langer T., Stuppner H. Strategies for efficient lead structure discovery from natural products. Curr Med Chem 2006, 13:1491-1507.
54. Viana A.F., Rates S.M.K., Naudin B., Janin F., Costentin J., Do Rego J.C. Effects of acute or 3-day treatments of Hypericum caprifoliatum Cham, & Schltdt. (Guttifereae) extract or of two established antidepressants on basal and stress-induced increase in serum and brain corticosterone levels. J Psychopharmacol 2008, 22:681-690.